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That’s just one of the questions that will likely be part of the chatter at Blogs with Balls 5, a sports media conference that brings some of the most interesting names in the online sports world from across North America to the TIFF Bell Lightbox this Friday and Saturday to chat IRL (in real life).

It’s the first time the conference takes place outside the U.S., thanks in part to The Score, which is sponsoring the event, with likely a little coaxing from The Basketball Jones guys, who have attended and been part of panels the past few years. They will be hosting a live edition of their podcast at the event on Saturday.

“The coolest part at the beginning was meeting all these people who you only had relationships with online. I would imagine that’s still the key, although it’s gotten much, much bigger,” says J.E. Skeets of TBJ, who first attended in 2009. “It’s like any conference, you know — the panels are the panels and that’s cool, but a lot of the really good stuff comes from networking after and grabbing a drink at the bar with someone who has reached a level you aspire to be at and pick their brain or grab a tip or two.”

The Basketball Jones should be the successful prototype for anybody with a blog or podcast. It started out as a passion project by obsessive fans, who lived and breathed basketball, and after years of work, networking and plenty of hilarious viral videos, it is now The Score’s crown jewel, and also provides content to Grantland and occasionally to NBA.com.

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While Canada’s sports media landscape has been reshaped through consolidation over the past two years, it’s down south where the really interesting online stuff is happening, and this conference brings many of those players to the city.

It’s interesting timing for The Score, which recently sold its television business to Rogers but will continue to focus on its app business and keeping its popular blogs, including TBJ and Drunk Jays Fans.

“There’s a very big sports blogging culture in Toronto and we thought it would be an interesting event to work with,” Jonathan Savage, The Score’s vice-president of marketing and social media, says of Blogs with Balls 5. “Our digital business being North American-focused, we thought it would great to associate ourselves with some emerging sports brands in the U.S.”

It’s clear the online world has mostly moved beyond the stereotype of the blogger in his basement, and these days, as soon as you get some kind of readership, you’re more likely to get scooped up by an established organization, similar to a record label signing an independent band.

Of course, that’s the basis of one of the big questions that Skeets wants to talk about with his contemporaries.

“I think it’s always interesting to chat about where it’s sort of going, and what’s next. Three years ago it was, ‘Can we actually make a living out of this? Will this stick around? Will blogs exist and will people pay for this?’ And now we know that it will,” he says.

“So what’s next? Is it these massive hubs like SB Nation? Is it impossible now to make it if you have your own single site? Just in terms of can it create enough revenue with ads and stuff, or will you have to be snatched up by one of these big companies?”

With panels covering everything from whether digital channels can challenge mainstream networks, a look at emerging digital initiatives, an NFL roundtable and the state of the hockey media (made all the more interesting with no hockey in sight), there’s something for every kind of web sports nerd out there.

For more information, check out blogswithballs.com. If you can’t make it — or balk at the $225 ticket price — Savage says the conference will be streamed online and there will likely be some Google Hangouts around some of the events.

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